92418-71-8

Basic information

• Product Name: (2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC)
• Synonyms: (2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC);(2R,3R)-(+)-3-propyloxiranemethanol;Oxiranemethanol,3-propyl-,(2R,3R)-(9CI);propyloxiranemethanol
• CAS NO: 92418-71-8
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.15828
• Product Categories: EPOXYDE
• Mol File: 92418-71-8.mol
• Article Data: 57

Chemical Properties

• Melting Point: 19 °C(lit.)
• Boiling Point: 31-33 °C0.35 mm Hg(lit.)
• Flash Point: 188 °F
• Appearance: /
• Density: 0.96 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.179mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• CAS DataBase Reference: (2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC)(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC)(92418-71-8)
• EPA Substance Registry System: (2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC)(92418-71-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 92418-71-8(Hazardous Substances Data)

Usage

General Description

(2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL is a chemical compound with a high purity level of 97% (94% EE/GLC). It is a chiral compound with two stereocenters, with the (2R,3R) configuration indicating the absolute configuration of the molecule. The chemical is used in various organic synthesis processes as a chiral building block or as a reagent in asymmetric synthesis. The high enantiomeric excess (EE) and gas-liquid chromatography (GLC) purity make it suitable for use in enantioselective reactions, where the stereochemistry of the compound is crucial for the desired outcome. Additionally, its propyloxirane functional group makes it versatile for use in the synthesis of complex organic molecules.

InChI:InChI=1/C6H12O2/c1-2-3-5-6(4-7)8-5/h5-7H,2-4H2,1H3/t5-,6-/m1/s1

Upstream product

• 928-95-0 (E)-2-Hexen-1-ol 
• 139164-92-4 (3R)-1-hexen-3-ol 
• 113566-32-8 (2S,3R)-3-Chlorotridecane-1,2-diol 
• 6728-26-3 (E)-2-Hexenal 
• 2305-21-7 2-hexen-1-ol 
• 220038-45-9 DIPT 
• 87-69-4 tartaric acid 
• 142204-60-2 (2S,3R)-3-benzoyloxy-1,2-hexanediol 
• 142204-61-3 (-)-(R)-hex-1-en-3-yl benzoate 
• 89321-71-1 (2S,3S)-3-propyl-2-oxiranemethanol 
• 113566-29-3 Ethyl (2S,3R)-3-chloro-2-hydroxytridecanoate 
• 113524-86-0 ethyl 3-chloro-2-oxotridecanoate 
• 475056-69-0 (2S,3R)-3-propyloxirane-2-carbaldehyde 
• 546-68-9 titanium(IV) isopropylate 

Downstream Products

• 145841-97-0 (2S,3R)-2-<(S)-(phenylsulfinyl)methyl>-3-propyloxirane 
• 145841-93-6 (2S,3R)-2-<(S)-(phenylsulfanyl)methyl>-3-propyloxirane 
• 94992-81-1 (2R,3R)-3-Methyl-hexane-1,2-diol 
• 693220-90-5 (2R,3S)-3-(3,5-dichloro-phenoxy)-hexane-1,2-diol 
• 693220-92-7 (2S,3S)-toluene-4-sulfonic acid 3-(3,5-dichloro-phenoxy)-2-hydroxy-hexyl ester 
• 693258-09-2 (2S,3S)-3-(3,5-dichloro-phenoxy)-1-methylamino-hexan-2-ol hydrochloride 
• 1166397-39-2 (2S,3S) 3-amino-2-hydroxy-hexanoyl cyclopropylamide hydrochloride salt 
• 959709-86-5 methyl (2S,3S) 3-amino-2-hydroxyhexanoate hydrochloride salt 
• 959740-13-7 methyl (2S, 3S)-3-amino-2-hydroxyhexanoate 
• 1023741-38-9 C₇H₁₄O₄S 
• 125414-29-1 (R)-1-((S)-2-Trichloromethyl-4,5-dihydro-oxazol-4-yl)-butan-1-ol 
• 125414-29-1 (S)-1-((R)-2-Trichloromethyl-4,5-dihydro-oxazol-4-yl)-butan-1-ol 
• 125414-42-8 ((1R,2R)-2-Hydroxy-1-hydroxymethyl-pentyl)-carbamic acid tert-butyl ester 
• 125414-42-8 ((1R,2S)-2-hydroxy-1-hydroxymethyl-pentyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

Solid-Phase Total Synthesis of Dehydrotryptophan-Bearing Cyclic Peptides Tunicyclin B, Sclerotide A, CDA3a, and CDA4a using a Protected β-Hydroxytryptophan Building Block

A new approach to the synthesis of Z-dehydrotryptophan (ΔTrp) peptides is described. This approach uses Fmoc-β-HOTrp(Boc)(TBS)-OH as a building block, which is readily prepared in high yield and incorporated into peptides using solid-phase Fmoc chemistry. The tert-butyldimethylsilyl-protected indolic alcohol is eliminated during global deprotection/resin cleavage to give ΔTrp peptides exclusively as the thermodynamically favored Z isomer. This approach was applied to the solid-phase synthesis of tunicyclin B, sclerotide A, CDA3a, and CDA4a.

Kinetic resolution of epoxy alcohols with the Sharpless Ti-isopropoxide/tartaric ester complex

When investigating the Sharpless epoxidation of enol-protected 4-hydroxy-1,2-cyclopentanediones, the ability of the asymmetric Ti(OiPr)4/tartaric ester complex to discriminate between enantiomeric epoxides formed in situ was discovered, leading to the epoxide opening reaction of only one enantiomer. This observation was used in the kinetic resolution of racemic substituted 2,3-epoxy-4-hydroxy-cyclopentanol, to afford enantiomerically enriched epoxyalcohols in good yields and with ees up to 96%.

Pore size matters! Helical heterogeneous catalysts in olefin oxidation

Helical mesoporous materials of the MCM-41 type with different pore sizes were prepared, choosing as templates myristyl (C14) or cetyl (C16) trimethyl ammonium salts, and functionalized with Mo(II) active sites based on MoI2(CO)3 (1) and MoBr(η3-C3H5)(CO)2 (2) fragments, respectively, using a pyridine-2-carbaldehyde ligand as anchor. The new materials were tested as the catalytic precursors in the epoxidation of cis-cyclooctene, styrene, R-(+)-limonene, trans-hex-2-en-1-ol, cis-3-hex-1-ol, and geraniol using tert-butylhydroperoxide (tbhp) as oxidant. All catalysts were moderately to highly selective toward the epoxide products. The materials with larger pores (C16 template) displayed a better catalytic activity, leading in general to higher conversions and selectivities, as well as faster kinetics. For instance, geraniol is epoxidized (more than 90%) with conversions above 90%. The major achievement of these catalysts, however, is the excellent product selectivity control, which is boosted when the allyl complex 1 is used, reaching 100% of the 2S, 3R species in the epoxidation of trans-hex-2-en-1-ol. The catalysts were also found to be stable through recycling experiments and truly heterogeneous with little or no leaching.